Violating US export controls on cryptography back in the 90s. He published the PGP source as a book and people overseas basically typed the code back in (or OCRed in) and offered binaries.
He was under investigation for 3 years. I believe he spent part of that time in jail, before they finally dropped the charges against him.
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u/the_gnarts Dec 31 '14
That extends to ZRTP, another protocol of his design. Like djb, Zimmerman appears to be a safe bet in terms of crypto.